Unsolvated homo- and heterometallic highly fluorinated β-diketonate complexes of copper(II)

Crowder, Janell M.; Han, Haixiang; Wei, Zheng; Dikarev, Evgeny V.; Petrukhina, Marina A.

doi:10.1016/j.poly.2018.09.048

Cited by 13 publications

(6 citation statements)

References 74 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The lowest electrostatic potential, shown in red, is around the oxygen atoms of Cu(L) 2 and EDOT. The highest electrostatic potentials of the centers of the pentafluorophenyl rings A-D are approximately +97, +90, +91, +83 kJ mol À1 , respectively, which is almost the same as the independently calculated value for Cu(L) 2 (+97 kJ mol À1 for the pentafluorophenyl ring), which was calculated using the currently reported crystal structure (Crowder et al, 2019). The lowest electrostatic potentials of the five-membered rings of EDOT are À77, À63, and À63 kJ mol À1 for EDOT-1, 2A and 3, respectively, indicating the electron distribution is slightly lower than that calculated independently for EDOT (À81 kJ mol À1 ) and used to estimate the intermolecular interactions of Cu(L) 2 and EDOT.…”

Section: Dft Calculationssupporting

confidence: 82%

Co-crystal structure, Hirshfeld surface analysis and DFT studies of 3,4-ethylenedioxythiophene solvated bis[1,3-bis(pentafluorophenyl)propane-1,3-dionato]copper(II)

2020

View full text Add to dashboard Cite

The title complex, Cu(L)2 or [Cu(C15HF10O2)2], comprised of one copper ion and two fully fluorinated ligands (L −), was crystallized with 3,4-ethylenedioxythiophene (EDOT, C6H6O2S) as a guest molecule to give in a dichloromethane solution a unique co-crystal, Cu(L)2·3C6H6O2S. In the crystal, the oxygen of one guest molecule, EDOT-1, is coordinated to the metal to give an alternate linear arrangement, and the π-planes of the others, EDOT-2 and EDOT-3, interact weakly with the pentafluorophenyl groups of the complex through arene–perfluoroarene interactions. Head-to-tail columnar and head-to-head dimeric arrangements are observed for EDOT-2 and EDOT-3, respectively, in the crystal. The Hirshfeld surface analysis indicated that the most important contributions for the crystal packing are from the F...F (20.4%), F...H/H...F (24.5%) and F...C/C...F (9.6%) interactions. The density functional theory (DFT) optimized structure at the ωB97X-D 6–31G* level was compared with the experimentally determined molecular structure in the solid state.

show abstract

Section: Dft Calculationssupporting

confidence: 82%

Co-crystal structure, Hirshfeld surface analysis and DFT studies of 3,4-ethylenedioxythiophene solvated bis[1,3-bis(pentafluorophenyl)propane-1,3-dionato]copper(II)

2020

View full text Add to dashboard Cite

show abstract

“…IR (KBr disk):

\overset{ν}{true}

=3445, 2936, 2361, 2342, 1622, 1562, 1520, 1501, 1175, 1090, 1015, 827, 669 cm −1 ; elemental analysis calcd (%) for C 34 H 4 Cu 2 F 20 O 6 : C 40.21, H 0.40; found: C 40.17, H 0.50. The single crystal of 2 was not obtained by using the standard methodology, which shows its high affinity towards guest encapsulation …”

Section: Methodsmentioning

confidence: 99%

Enhanced and Heteromolecular Guest Encapsulation in Nonporous Crystals of a Perfluorinated Triketonato Dinuclear Copper Complex

Ikumura

Habuka

Sakai

et al. 2020

Chemistry A European J

View full text Add to dashboard Cite

The flexible hostf ramework of ap erfluorinated mononuclear copper complex,[ Cu(L 1 ) 2 ]( 1,H L 1 = 3-hydroxy-1,3-bis(pentafluorophenyl)-2-propen-1-one), with aC uO 4 core reversibly encapsulateds everal organic guest molecules throughe lectrostatic interactions in its crystals. Hence, the correspondingd inuclearc omplex, [Cu 2 (L 2 ) 2 ]( 2,H 2 L 2 = 1,5-dihydroxy-1,5-bis(pentafluorophenyl)-1,4-pentadien-3-one), was prepared to enhanceg uest recognition and the ability to separate molecular mixtures. Complex 2 comprises a Cu 2 O 6 core and four pentafluorophenylg roups. In crystal 2, cavitiesa re formed on the axial sites of the metal core that are surroundedb yp entafluorophenylg roups.T he crystal of 2 encapsulates various guest molecules, that is, benzene (3), toluene (4), xylene (5), mesitylene (6), durene (7), and anisole (8). X-ray crystallographic and thermogravimetric (TG) studies show that three guest molecules are present in the crystal cavities. The number of guest molecules found in complex 2 was higher than that in complex 1,f or example, (2) 3 ·(6) 10 > 1·(6) 2 ,( 2) 2 ·(7) 7 > 1·7,o r2·(8) 3 > 1·(8) 2 .N aphthalene (9), was encapsulatedi n2 to give 2·(9) 3 ,b ut not in 1.I nt he crystal of complex 2,h eteromolecular guest encapsulation was confirmed, designated as 2·(3) 2 ·9.T Ga nalysis indicates that the thermals tabilityo ft he guest-included crystalso f2 is higher than that of 1. Figure 11. TG curves of guestrelease from 2·(3) 3 , 2·(9) 3 ,a nd 2·(3) 2 ·9.The scan rate was 5.0 8Cmin À1 .

show abstract

“…[Cu(L CF3 ) 2 (THF)] is a square pyramidal complex with an apical THF ligand. Such square pyramidal diketonate molecules are very rare in copper(II), and the copper(II) complex [Cu(L C6F5 ) 2 (OH 2 )] derived from the deprotonated 1,3-bis(pentafluorophenyl)propane-1,3-dione (HL C6F5 ) is the only other structurally characterized example in the literature, to our knowledge [89] 12) was synthesized in a water/ethanol solution, using zinc(II) chloride and NaL Mes precursors. The IR spectra were carried out on solid samples of 7-12.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Synthesis and Investigations of the Antitumor Effects of First-Row Transition Metal(II) Complexes Supported by Two Fluorinated and Non-Fluorinated β-Diketonates

Pellei,

Del Gobbo,

Caviglia

et al. 2024

IJMS

View full text Add to dashboard Cite

The 3d transition metal (Mn(II), Fe(II), Co(II), Ni(II), Cu(II) and Zn(II)) complexes, supported by anions of sterically demanding β-diketones, 1,3-dimesitylpropane-1,3-dione (HLMes) and 1,3-bis(3,5-bis(trifluoromethyl)phenyl)-3-hydroxyprop-2-en-1-one (HLCF3), were synthesized and evaluated for their antitumor activity. To assess the biological effects of substituents on phenyl moieties, we also synthesized and investigated the analogous metal(II) complexes of the anion of the less bulky 1,3-diphenylpropane-1,3-dione (HLPh) ligand. The compounds [Cu(LCF3)2], [Cu(LMes)2] and ([Zn(LMes)2]) were characterized by X-ray crystallography. The [Cu(LCF3)2] crystallizes with an apical molecule of solvent (THF) and features a rare square pyramidal geometry at the Cu(II) center. The copper(II) and zinc(II) complexes of diketonate ligands, derived from the deprotonated 1,3-dimesitylpropane-1,3-dione (HLMes), adopt a square planar or a tetrahedral geometry at the metal, respectively. We evaluated the antitumor properties of the newly synthesized (Mn(II), Fe(II), Co(II), Ni(II), Cu(II) and Zn(II)) complexes against a series of human tumor cell lines derived from different solid tumors. Except for iron derivatives, cellular studies revealed noteworthy antitumor properties, even towards cancer cells endowed with poor sensitivity to the reference drug cisplatin.

show abstract

Unsolvated homo- and heterometallic highly fluorinated β-diketonate complexes of copper(II)

Cited by 13 publications

References 74 publications

Co-crystal structure, Hirshfeld surface analysis and DFT studies of 3,4-ethylenedioxythiophene solvated bis[1,3-bis(pentafluorophenyl)propane-1,3-dionato]copper(II)

Co-crystal structure, Hirshfeld surface analysis and DFT studies of 3,4-ethylenedioxythiophene solvated bis[1,3-bis(pentafluorophenyl)propane-1,3-dionato]copper(II)

Enhanced and Heteromolecular Guest Encapsulation in Nonporous Crystals of a Perfluorinated Triketonato Dinuclear Copper Complex

Synthesis and Investigations of the Antitumor Effects of First-Row Transition Metal(II) Complexes Supported by Two Fluorinated and Non-Fluorinated β-Diketonates

Contact Info

Product

Resources

About